Azo dyestuffs and fiber dyed therewith



Patented Dec. 26, 1933 v UNITED?" STATES \AZODYESTUFFS mrmnm- 1 THEREW ITHl Q5 Ernst Ruime and Karl Moldaenke, Frankfort-om 1 the-Main-Hochst, and Wetner Kirst, Frankporation .0: Delaware fort-on-the-Main, Germany, assig'nnrs to General Aniline Works, Inc New York, N; Y., a corv No Drawing. Application November 10, 1928, Serial No. 318581, and invGermany November -14, 1927 ZQClair'ns.

The present invention relates to new waterinsoluble azo dyestuffs and to fiber dyed therewith. We have found that water insoluble azo dyestuifs of a brightness not'lyet attained and of valuable properties as to fastness are obtained, by diazotizing a compound of the general formula:

([3113 x NH;

X 1130 CH| wherein X represents chlorine bromine or a nitro group, and coupling it with an arylamide of 2.3

. by wringing out or hydrorextracting and dyed in the dye-bath for hour. The dyed material is rinsed, soaped at the boil, again rinsed and dried.

1. (a) Grounding liquor I 4.5 grammes of 2.3 hydroxynaphthoic acid-2- methyl-4'-chloro-1-anilide are made into a paste with 9 com. of sodium Turkey red oil of 50% strength andQccm. of caustic soda'solution of 34 B,:this paste is covered by pouring boiling (onomo water over it and dissolved "while bo'iling, if iequired, so as to give]. liter. 7 i y -(b) Dye bath 1.84 grammes of2-amino-5-chloro-1-methy1-4- nor with 2.6 ccmfof hydrochloric acid of 22 B- and 0.72 grammes of dissolved sodium nitrite while cooling with ice After the diazotization is complete, the diazo compound is neutralized by means of 2 grammes of dissolved sodium acetate, there are then added 25 grammes of sodium chlorideand the whole is made up with cold water to 1 liter. I The dyeing has a vivid; bluish-red, shade, fast to men-boiling. .The dyestufi has the formula:

OH; on, r \d :CHi.

Q 2.10;) liquor I 3.6 grammes ofdiacetoacetic acid-ortho tolidide are dissolved; while. heating, "with 7.2

grammes of Turkey redjoiI; 5.4 ccm. of caustic soda solution of 34 B and 28 grammes of sodium sulfate so astogivel liter.

@w ww This is prepared in the same manner as that of 'Example 1, except that there .are finally added 2' com. of aceticiacid' of 50% strength; 1

The dyeing has a reddish-yellow shade fast .to

light and to kier-boiling.

ably the formula v11,0 v on;

CH: CH:

4.5 grammes of 2.3 hydroxynaphthoic acid-4'- The dyestuft ihas'probmethoxy-1'-anilide are made into a'paste with 9 room. of Turkey redoil of 50% strength? and 10.5

55- isopropyl'e'b'enzene are diazotized' in the'usualmancbmt of caustic soda solution of 34.Bi this paste 116 boiling, so as to give lliter: u

is poured over with water and dissolved, While 2. The water-insoluble azo dyestuffs of the while cooling with ice.

(b) Dye both CTHa The tints of furtherdyestuifs of the new type herein claimed are stated'in the following table:

following formula:

on. cm

v Y wherein .1; stands for halogen, Y stands for hydrogen, --CH3 or --OCH3 and Z stands for hy- 0 drogen or halogen.

3. The water-insoluble azo dyestufis of the following formula CH3 CH3 j g c5 OH H I C: wherein Y stands forhydrogen, CH3 or OCH2 and Z stands for hydrogen or chlorine.

Combined with the 4. The water-insoluble azo dyestuffs of the following arylamide Shade of the followin formula Diazo compound from of gfiihydmxynapb dyeing g CH3 CH3 7 thou: acid Y 7 V X CH 2-amino-5-oh1oro-1 2-methoxy-4-ch1oro- Scarlet V V methyl 4 isopro 1'-anllide 1 N=N X pylbonzene I Do. 2'5 dimetlioxy l Blulsh-red 0H anilide H36 X Do *ortho-anisidide Scarlet Do. OI'thO-fnlnidirln Bluish-scarlet Do a-naphthy mi n Bluish-red Do di-ottho-anisidide Bordeau-red \CQ NH C1 2 amino 6 nitro '-1 ortlio-anisidide Yellowish-red methyl 4 isopro 1 meme 2' th 1: 151 s It l t Y O -me QXY -0 010- care Y-anili e wherein X stands for chlorine, bromine or a, nitro f' fffigi fiz' f a group, and Y stands for CH3 or -OCH3. r V

' 'di-ortho-anisidide Reddish-orown w 5. The water-insoluble azo dyestuffs of the fol- V lowing formula V e A V CH3 CH3 r r 3 The tints obtained from diazotized 2-am1no-5- V .bromo-1-methyl-4-isopropylbenzene and an 7 N N O1 Jv arylamide of -2.3-hydroxy-naphthoic acid are r very similar to the corresponding dyestuffs ob- 0H CH 1 tained from the fi-chloro-derivative. r 13G We claim: 1. The water-insoluble azo. dyestuffs of the CQ NH l following formula wherein Y stands for OCH3 or -CI-Ia.

. 6. The water-insoluble azo dyestuffs of the following formula CH:\ /GH: x OH V r N===N x OH Z V 7 0H:

' 7 \oO-NHQOI wherein X stands for chlorine, bromine or a nitro I a group, Y stands for. hydrogen, CH or 0c1-I whereinXstands for chlorine, bromine or a nitro and Z stands for hydrogen or halogen.

group.

'7. The water-insoluble azo dyestuff of the following formula 'CH;\ CH: 0

, eo-NEF-Qm CH: having a vivid, bluish-red shade, fast to kierboiling.

8. The water-insoluble azo dyestuffs of the following formula:

wherein X stands for chlorine, bromine or a nitro group and R represents a radical of the benzene or naphthalene. series.

9. The water-insoluble azo dyestuffs of the following formula:

C0-NH-R wherein X stands for halogen, and R. represents 7 claim 1.

a radical of the benzene or naphthalene series. 10. The water-insoluble azo dyestuffs of the following formula:

as claimed in dyed with dyestuffs as claimed in dyed with dyestuffs vas claimed in dyed with dyestuffs as claimed in dyed with dyestufis as claimed in dyed with the dyestuff as claimed in dyed with dyestuffs as claimed in dyed with dyestufis as claimed in claim9.

19. Fiber claim 10.

20. Fiber dyed with dyestuffs as claimed in dyed with dyestuffs as claimed in ERNST RUNNE.

KARL MOLDAENKE. WERNER KIRST. 

